| 2026-09-13 | Chicago FirevNew England RevolutionMLS · United States | 1–2 | MLS · United States |
| 2026-09-13 | Chicago FirevNew England RevolutionMLS | 1–2 | MLS |
| 2026-09-10 | Chicago FirevInter MiamiMLS · United States | 1–1 | MLS · United States |
| 2026-09-10 | Chicago FirevInter Miami CFMLS | 1–1 | MLS |
| 2026-09-06 | Toronto FCvChicago FireMLS · United States | 4–4 | MLS · United States |
| 2026-09-05 | Toronto FCvChicago FireMLS | 4–4 | MLS |
| 2026-08-29 | Seattle Sounders FCvChicago FireMLS | 2–2 | MLS |
| 2026-08-29 | Seattle SoundersvChicago FireMLS · United States | 2–2 | MLS · United States |
| 2026-08-26 | MonterreyvChicago FireLEAGUESCUP | 2–1 | LEAGUESCUP |
| 2026-08-23 | New York Red BullsvChicago FireMLS · United States | 1–1 | MLS · United States |
| 2026-08-22 | New York Red BullsvChicago FireMLS | 1–1 | MLS |
| 2026-08-20 | Orlando CityvChicago FireMLS · United States | 1–2 | MLS · United States |
| 2026-08-19 | Orlando City SCvChicago FireMLS | 1–2 | MLS |
| 2026-08-16 | Chicago FirevPortland TimbersMLS · United States | 2–1 | MLS · United States |
| 2026-08-16 | Chicago FirevPortland TimbersMLS | 2–1 | MLS |
| 2026-08-16 | Chicago FirevPortland TimbersMLS | 2–1 | MLS |
| 2026-08-14 | Cruz AzulvChicago FireLEAGUESCUP | 1–2 | LEAGUESCUP |
| 2026-08-10 | Chicago FirevSantosLEAGUESCUP | 3–1 | LEAGUESCUP |
| 2026-08-07 | Chicago FirevNecaxaLEAGUESCUP | 2–0 | LEAGUESCUP |
| 2026-08-02 | Chicago FirevCharlotteMLS · United States | 2–1 | MLS · United States |
| 2026-08-02 | Chicago FirevCharlotteMLS | 2–1 | MLS |
| 2026-07-26 | New York CityvChicago FireMLS · United States | 3–1 | MLS · United States |
| 2026-07-23 | Inter MiamivChicago FireMLS · United States | 3–2 | MLS · United States |
| 2026-05-24 | Chicago FirevToronto FCMLS · United States | 2–1 | MLS · United States |
| 2026-05-16 | CF MontrealvChicago FireMLS · United States | 0–2 | MLS · United States |
| 2026-05-14 | DC UnitedvChicago FireMLS · United States | 1–3 | MLS · United States |
| 2026-05-09 | Chicago FirevNew York Red BullsMLS · United States | 1–3 | MLS · United States |
| 2026-05-03 | Chicago FirevFC CincinnatiMLS · United States | 2–3 | MLS · United States |
| 2026-04-26 | Chicago FirevSporting Kansas CityMLS · United States | 5–0 | MLS · United States |
| 2026-04-19 | FC CincinnativChicago FireMLS · United States | 3–3 | MLS · United States |
| 2026-04-12 | Chicago FirevAtlanta UtdMLS · United States | 1–0 | MLS · United States |
| 2026-04-05 | Chicago FirevNashville SCMLS · United States | 1–0 | MLS · United States |
| 2026-03-21 | Philadelphia UnionvChicago FireMLS · United States | 1–2 | MLS · United States |
| 2026-03-15 | Chicago FirevDC UnitedMLS · United States | 1–2 | MLS · United States |
| 2026-03-08 | Columbus CrewvChicago FireMLS · United States | 0–0 | MLS · United States |
| 2026-02-28 | Chicago FirevCF MontrealMLS · United States | 3–0 | MLS · United States |
| 2026-02-22 | Houston DynamovChicago FireMLS · United States | 2–1 | MLS · United States |
| 2025-11-01 | Chicago FirevPhiladelphia UnionMLS · United States | 0–3 | MLS · United States |
| 2025-10-26 | Philadelphia UnionvChicago FireMLS · United States | 2–2 | MLS · United States |
| 2025-10-23 | Chicago FirevOrlando CityMLS · United States | 3–1 | MLS · United States |
| 2025-10-18 | New England RevolutionvChicago FireMLS · United States | 2–2 | MLS · United States |
| 2025-10-05 | Chicago FirevToronto FCMLS · United States | 2–2 | MLS · United States |
| 2025-10-01 | Inter MiamivChicago FireMLS · United States | 3–5 | MLS · United States |
| 2025-09-28 | Chicago FirevColumbus CrewMLS · United States | 2–0 | MLS · United States |
| 2025-09-21 | Minnesota UnitedvChicago FireMLS · United States | 0–3 | MLS · United States |
| 2025-09-14 | Chicago FirevNew York CityMLS · United States | 1–3 | MLS · United States |
| 2025-09-07 | Chicago FirevNew England RevolutionMLS · United States | 3–2 | MLS · United States |
| 2025-08-24 | Philadelphia UnionvChicago FireMLS · United States | 4–0 | MLS · United States |
| 2025-08-17 | Chicago FirevSt. Louis CityMLS · United States | 3–2 | MLS · United States |
| 2025-08-10 | Chicago FirevLos Angeles FCMLS · United States | 2–2 | MLS · United States |